Caddyshack
by MaxGentlman1
Summary: When the power goes off at the Odyssey and Fish Stick on a Stick again, Penn decides to treat Boone and Sashi to a game of golf. When the country club's groundskeeper is severely injured by Boone, the trio must save him by entering a golf tournament.
1. Chapter 1

**-7:58 AM, Saturday-**

Usually, kids slept in on Saturdays after waking up at 6:00 AM five times a week. For Penn Zero however, he had to wake up around this time to get ready for his job. Now for kids his age, that would be something like working the register at fast-food joint or be a stock boy at some store. Penn, he had a different kind of job; he was a part-time hero. His alarm struck 8:00 AM and music began to play over it as Penn began to stir from his sleep.

 **I'm alright**  
 **Nobody worry 'bout me**  
 **Why you got to gimme a fight**  
 **Can't you just let it be**

 **I'm alright**  
 **Don't nobody worry 'bout me**  
 **You got to gimme a fight**  
 **Why don't you just let me be**

Penn got out of bed and went to the bathroom and brushed his teeth. He looked in the mirror and ran his fingers through his curly red hair before going back to his room and got dressed for the day.

 **Do what you like**  
 **Doing it nat'rally**  
 **But if it's too easy**  
 **They're gonna disagree**

 **It's your life**  
 **And isn't it a mystery**  
 **If it's nobody's bus'ness**  
 **It's everybody's game**

After putting on his signature shirt, brown pants, and blue sneakers, he ran down the stairs and into the kitchen where his Uncle Chuck and Aunt Rose were sitting at the table eating breakfast. He didn't stop to chat, he merely grabbed a slice of toast and gave them a morning hug before rushing out the back door and towards the Odyssey.

 **Gotta catch you later**  
 **No, no, cannonball it right away**

 **Some Cinderella kid**

 **Get it up and get you a job**  
 **(Dip, dip, dip, dip, dip, dip, dip, dip)**

Meanwhile, at an apartment building not too far from Penn's house, a young girl about Penn's age was getting up and ready for the day as well. She had brown hair that she wore in two ponytails and a purple dress and blue glasses with mismatching socks. Her name was Sashi Kobayashi, Penn's part-time sidekick and one of his best friends.

 **I'm alright**  
 **Nobody worry 'bout me**  
 **Why you got to gimme a fight**  
 **Can't you just let it be**

 **I'm alright**  
 **Don't nobody worry 'bout me**  
 **You got to gimme a fight**  
 **Why don't you just let me be**

 **Who do you want**  
 **Who you be today**  
 **And who is it really**  
 **Makin' up your mind**

She ran out of her room and gave a quick good morning hug to her mom and dad and ruffled her little brother's hair before grabbing an apple from the fruit bowl and running out the door.

 **You wanna listen to the man**  
 **Pay attention to the magistrate**  
 **And while I got you in the mood**  
 **Listen to your**

When she saw the hallway was clear, she ran to a nearby window, opened it, and jumped to a nearby tree branch before swinging around it and hopped down to the ground and landing perfectly before running off to her job at the Odyssey as well.

 **Own heart beatin'**  
 **Own heart beatin'**  
 **Own heart beatin'**  
 **Own heart beatin'**

 **Don't it get you movin'**

 **Mmmmm-man**

 **It make me feel good**

 **(Wow, Cinderella kid)**

 **Then give it up and give it the job**

 **(Dip, dip, dip, dip, dip, dip, dip, dip)**  
 **(Boom, boom, boom, boom)**

At the very same time, a portly boy the same age as Penn and Sashi was getting dressed and heading out the door after saying good morning to his family. He wore a backwards baseball cap, brown cargo shorts, a green and brown striped tank top, and flip-flops. The boy's name was Boone Wiseman, Penn's best friend and part-time... well, wise man.

 **I'm alright**  
 **Nobody worry 'bout me**  
 **Why you got to gimme a fight**  
 **Can't you just let it be**

 **I'm alright**  
 **Don't nobody worry 'bout me**  
 **You got to gimme a fight**  
 **Why don't you just let me be**

The three were running down three separate sidewalks before they met at an intersection and began to race each other to the Odyssey.

 **I'm alright**  
 **Nobody worry 'bout me**  
 **Why you got to gimme a fight**  
 **Can't you just let it be**

 **I'm alright**  
 **I'm alright**  
 **Just let me be**

They were all neck-and-neck when Penn pulled ahead at the last minute. He was about to get inside when he suddenly hit the door to the theater and falling to the ground. Confused by this and picking himself up off the ground, Penn tried to open the theater door again and found it completely locked.

"The heck?" Penn asked out loud. As if to answer his question, they found their boss Phylis sitting on the sidewalk along with Phil, the boss of Larry and Rippen, the part-time villains, who had just arrived to the exact same result.

"Phylis, what's going on? Why are the doors locked?" Penn asked.

"Blew fuse again. Power out in both places. No missions today." She said.

"Seriously, again?" Boone asked.

"Well now what?" Rippen asked no one in particular.

"Oh, oh, we can go to my house again!" Larry said excitedly.

"No!" Everyone collectively yelled. After the last time they spent at Larry's house, they'd rather not go through a similar debacle.

"Well, guess we'll just find something else to do; come on guys." Penn said, leading his two friends away from the theater and leaving the part-time villains, who left in the opposite direction.

* * *

After an hour of wandering around Middleburg looking for something to do after a few failed attempts that included Boone suggesting they go to an arcade which resulted in Sashi breaking the punching bag game and being kicked out by the owner and Sashi suggesting they try the gym but her friends were to lazy for anything strenuous that didn't involve being zapped into another dimension.

When the trio finally ran out of options, an idea came to Penn like a bolt of lightning.

"Hey guys, I think I have an idea." He told his partners.

His idea for an activity surprised his friends quite a bit. 'What was his idea?' you ask? Golf.

After the three teenagers changed into more appropriate clothing for the sport, they made their way to the Middleburg Country Club.

"I have to tell you P.Z., I'm a little surprised you chose golf of all things." Sashi told her friend.

"Yeah, well, it's a bit of a hobby actually," He told his violent friend, "My dad took me here a few times when I was younger and before he and mom were trapped in The Most Dangerous World Imaginable."

"Were you any good?" She asked.

"You'll just have to see for yourself." He said with a small smirk.

The trio soon came to a chain-link fence that surrounded the club's golf field. After sneaking up to the gate, Penn halted them with a raised hand.

"Okay, now to contact my man on the inside. HEY, CRAZY LOUIS!" He yelled. Almost immediately, a rather disheveled-looking man with a bony figure and lazy eyes and wearing jeans, a tank top, and a sun hat came to the gate.

"Oh hey Penn, how's things going." He said nonchalantly as he let the trio in. As they walked through the gate and past the odd groundskeeper, Sashi grabbed Penn's arm and leaned into his ear.

"Hey, P.Z., can we trust this guy?" She asked.

"Who? Crazy Louis? Oh, he's fine, he's just a little..." He trailed off as the two looked back at him to see him doing a little jig while whistling to himself a nonsense tune.

"Crazy?" Sashi asked.

"I was gonna say 'stark raving gazonkers', but that works too." He said before they continued into the grounds.

* * *

 **-Hole 1-**

"Now, watch and learn. Ball bounces off the tree, careens off the passing eagle and into the hole." Penn said confidently.

"You are such a show-off." Sashi commented.

"I am not showing off," Penn said before putting on a blindfold, " _Now_ I'm showing off. 1, 2, 3, golf shot!" He exclaimed, striking the ball which bounced of a nearby tree and flew into the air which hit a bird in the chest, causing it to squawk, before finally landing perfectly in the hole. Boone and Sashi applauded Penn's amazing trick shot as he took off his blindfold and did an exaggerated bow.

"Hey, Penn, can you teach me how to play like that?" Boone asked eagerly.

"Sure, why not?" Penn said as he gave Boone a club and set up another ball.

"Okay, now first: Empty your mind." Penn instructed.

"Done." Boone said immediately.

"Wow, that was easy." Penn commented before grabbing Boone and getting on their hands and knees and getting eye-level with the ball "Second, get to know your target. _Be_ the ball. _Feel_ the ball." He was saying until he saw Boone opening his mouth, "No, don't eat the ball." He deadpanned.

"Sorry." The part-time wise man apologized as they both got back to their feet.

"Alright." Penn started, "Now, shoulders back," He said and Boone did so, "butt clenched," Boone did that as well, "and just listen to that little voice in your head that tells you to SWING!" He yelled, surprising Boone and causing him to swing the club and send it flying out of his hands. The club flew nearly twenty feet until it struck Crazy Louis, who was watering the grass, in the back, causing him to fall to the ground in pain.

"Oh my gosh, Crazy Louis!" Penn yelled as he, Boone, and Sashi ran to his aid.

"Ow, my appendix. How will I be able to process enzymes and convert them into simple sugars?" He asked in pain.

"Wait, how do you know it's you appendix?" Penn asked.

"Well if you look at this x-ray," He said, taking out an x-ray from seemingly nowhere, "my appendix, that's this right here, was on it's last legs so to speak. The doc said I'd be fine as long as no one hit it with a golf club."

"That is an oddly specific diagnosis." Penn commented as Crazy Louis groaned in pain.

"Don't worry about me though, guys, I've lived a good life." He said weakly.

"Well he's a goner, shall we get back to the game?" Sashi said, not really caring and walking off when Penn grabbed her by the arm.

"Sashi, we just can't leave him here to die. We have to help him somehow. But how?" He asked as he began to think.

"We could just enter that golf tournament over there." Boone said offhandedly, pointing to a banner off in the distance.

"Middleburg Annual Golf Tournament. First Prize: One Appendix." Penn read, "Well that's convenient. Weird, but convenient. Sashi, stay with Crazy Louis while Boone and I enter the tournament to win that appendix. Don't worry, Louis, I shall return!" Penn said before he and Boone ran off.

* * *

 **This is a two-shot story. Hope you guys enjoyed the first half, I'll post the second half sometime soon. And if you guys are wondering, the song played at the beginning was "I'm Alright" by Kenny Loggins.**


	2. Chapter 2

**Welcome to part two. Hope you guys (or girls, let's not judge) enjoy!**

* * *

 **-Tournament-**

The golf tournament had quite an audience gathered to see the game, it was even being covered by local television. A small camera crew was gathered around the sign-up station as people entered.

"Hello, this Donald Dahl coming to you live from the Middleburg Country Club where dozens of fans have gathered and entered to see this classic sport." The reporter spoke to the camera, "The weather is beautiful here today and the competition will be fierce as some of Middleburg's top golfers have entered. Let's see if we can get a comment from one of the entries. Excuse me," Donald said, stopping Penn and Boone as they walked by, "How do feel about your chances of winning?"

"Well I don't want to blow my own trumpet," Penn said, feigning modesty, "But I'd say my chances are pretty good."

"Well that is quite the confident thing to say, especially given your competition." Donald commented.

"And who's that?" Penn asked.

"That would be me, Penn Zero." Came an all to familiar English accent. Turning around, Penn and Boone came face to face with Rippen and Larry, both wearing golf uniforms while Larry carried a bag of golf clubs.

"Rippen, what are you doing here?" Penn asked.

"Well, my ginger adversary, if you must know I was planing to attend this tournament some time ago but unfortunately it coincided with a work day. But, by a pure stroke of luck, the power got cut off so now I'm free to enter and win." The part time villain explained.

"Well that will be kinda hard seeing as how I'm gonna win this thing." Penn challenged.

"We shall see about that. Come along, Larry." Rippen said before leaving with Larry pleasantly waving goodbye.

"Think we can beat him?" Boone asked. After a couple of seconds of silence the two then burst into a fit of laughter at the question. They soon calmed down as they both wiped a tear away.

"Don't worry, Boone, I got this. Wait for me by the first hole, I gotta make a call." Penn said, taking out his cellphone and calling Sashi, "Sashi, how's our patient holding up?"

"Not too good I'm afraid." The part time sidekick said on the other end of the line as she looked after Crazy Louis.

"I am the mayor of Butter Town; all rise for our national anthem! **_Oh Butter Town, your creamy streets of gold~._** "

"I don't think he is the mayor of Butter Town." Sashi whispered into her phone.

"Just keep him alive, Sashi. Alive!" He said before hanging up, "Alright, let's play some golf." He said nonchalantly, throwing his phone over his shoulder.

* * *

 **-Hole 1-**

Rippen was up first to tee off. He lined up his shot and hit so that it landed right on the green just a few feet from the hole.

"Take that, you insufferable buffoon." Rippen insulted Penn with a smirk.

"A delicious shot indeed, almost like some sort of delicious meat pie." Penn retorted in an insulting British accent that made Rippen fume as Penn and Boone got ready for their turn.

"So what do you think, Boone?" Penn asked his wise man turn caddie.

Boone place his index finger in his mouth and took it out, thinking for a second before saying "My finger tastes like pancakes."

"Seven iron it is. One, two, three, golf shot!" Penn said, taking the club, lining up his shot and striking it with great force. The ball bounced off a tree and into the air where it struck the very same eagle from earlier in the spleen before it fell straight into the hole, causing the crowd to cheer and applaud the part time hero's shot. Even Larry was applauding the shot before Rippen gave him a death glare, causing the part time villain's henchman to smile sheepishly.

"Lucky shot. Come, Larry." Rippen said dismissively as he and Larry boarded a golf cart with Larry at the wheel before they drove of to the next hole backwards.

* * *

The tournament continued with Penn easily making each hole in one or two shots and Rippen in a distant second. They soon came to the tenth hole where Rippen and Larry soon arrived with the cart still going in reverse.

"Larry, why do you keep driving this thing backwards?" Rippen asked his number two.

"Sorry, Rippen, there's just so many buttons." The short and pudgy henchman said. Rippen looked at the cart's dashboard to find that there were only two buttons, a green one marked "Forward" and a red one marked "Reverse". Rippen just gave a deadpan expression before face-palming his henchman's total incompetence.

Penn soon came up for his turn as he readied his ball and positioned himself. Rippen however, being the villain that he was, had different plans.

"Hey, what's that up there?!" He exclaimed, pointing up in the sky and causing everyone to look to where he was pointing. While everyone was distracted, he switched Penn's ball out with one that would explode on contact with his club. Giving a sinister snicker at his evilness, he got back to his feet and back to where he was standing.

"My mistake, it was just a helicopter." He lied as everyone returned their attention to the game. Knowing that Rippen had probably done something, Penn had idea of his own. He swung his club but missed it completely,"Whoops, I missed." He said before taking another swing and missing again,"Whoops, missed again." He took yet another swing and missed a third time,"Wow, this just isn't my hole."

He continued to miss the ball until Rippen grew frustrated with the part-time hero's missing,"Look!" He said in annoyance, walking up and taking the club from Penn's hands, "Like this!" He yelled as he hit the ball and causing it to explode in his face, covering him in soot.

"...Ow..." Was all he said before Penn walked up and took his club back and retook his shot, getting another hole in one.

* * *

 **-Hole 14-**

Hole 14 was a somewhat tricky section. The hole lay on the other side of a very wide lake which you'd be lucky to get to the opposite side of. Penn set up his ball and then struck it, causing it to land just at the edge of the pond. Rippen using his villainous genius, snuck up to Penn's ball from behind a nearby bush and hit the ball with the grip of his club like a pool cue, sending the ball into the water.

"Oh, a bit of bad luck for competitor Penn Zero. That will cost him a stroke." Donald Dahl said.

"Dang it. Boone, any ideas?" Penn asked.

"Well, I would suggest you use one of those golf club thingies, and this old-timey diving suit." The wise man turn caddie said.

"Well this is truly an astonishing turn of events. It seems that Penn Zero is going to take his shot from the bottom of the lake." Dahl said in amazement.

Penn floated to the bottom of the lake where he found his ball on the lake bed. Lining up his shot, he hit the ball and it flew through the water, onto the shore and into the hole. Rippen just gritted his teeth in frustration at his attempts at cheating were failing.

* * *

 **-Hole 17-**

The tournament has finally come to the second to last hole of the game. Penn had just hit his ball and it landed on the green where with a simple tap of a putter would get him a birdie. Rippen was still extremely frustrated at losing to the part-time hero again as he and Larry sat in their golf cart. Penn was about to take his shot when Larry spoke up to Rippen.

"Hey, Rippen, I finally figured out how to make this cart go forward." He said, pressing the green "Forward" button and causing the the golf cart to speed forward and run Penn over and causing all the onlookers to gasp.

"What a shocking development! It seems that the current lead, Penn Zero, had just been run over by a golf cart... What's up with that?" Dahl asked the camera.

"Oh my gosh, Penn, are you alright?!" Boone asked his flattened friend.

"My everything hurts." Penn answered weakly.

"Can you still play?"

"I just got crushed by a golf cart, Boone, what do you think?" The part-time hero asked rhetorically.

"Ha-ha, he's unable to play, that means I win by default!" Rippen exclaimed.

"Not so fast! According to the official rule book..." Donald trailed off as he began to flip through the pages one at a time.

 **-Two Hours Later-**

Donald was still flipping through the pages of the rule book as any and all attendants had tired and bored looks on their faces.

"... Ah, here we go... No, wait, that's the wrong page." Donald said before continuing to flip through the pages.

"Oh my god, this guy is even more boring than Larry." Rippen groaned.

"Tell me about it." Penn replied, standing next to Rippen in various casts and propped up with crutches.

"Here we go!" Donald said, finally finding the right page, "According to the rules: If a competitor is unable to continue playing, his caddie shall take his place."

"Wait, I have to play?!" Boone asked with slight worry.

"Don't worry, Boone, you got this. We have a two hundred stroke lead, there's no way we can lose." Penn said with confidence.

* * *

Boone took up his position next to the ball and gently tapped it but barely missed the hole.

"Whoops. Do-over." He said before tapping the ball again and missing again, "Let me try again." Again he tapped the ball and once again he missed, "Man, this is harder than it looks."

 **-196 Strokes Later-**

Finally, Boone knocked the ball into the hole.

"Yes, I'm the man!" He said triumphantly.

"Boone, you just wiped out a two hundred stroke lead." Penn said in disbelief.

"And that's...?" Boone trailed off.

"Bad." Penn deadpanned.

"Bad, right." Boone in understanding.

* * *

 **-Hole 18-**

"Here we are, ladies and gentlemen, Hole 18. After Penn Zero's caddie knocked out the impressive lead that they had acquired, the only way for them to possibly win this tournament now would be if he got a hole in one." Donald commentated.

"Don't worry, Boone, I have faith that you can do this." Penn encouraged as Boone took his position.

"Just give up now; save us the trouble." Rippen called from his spot in the crowd.

"Don't listen to him, Boone. Just remember what I taught you." Penn said.

"Right, just remember what he taught you... What was that though?" Boone said to himself, "Be the ball, fear the ball? No. Be the ball, eat the ball? No, that wasn't it either. Come on, Wiseman, think!"

While Boone tried to remember Penn's words, the eagle from earlier that day flew overhead, carrying a golf ball in its talons before dropping it and making it land on Boone's head, knocking him out cold.

 **-Inside Boone's Head-**

Boone found himself in a trippy dream where he hatched from a golf ball in front of a giant Penn that looked like Buddha.

 _"Whoa there, young Wiseman, looks like you got conked on the head but good. Be that ball, feel that ball. Whoa, I gots to go, young Wiseman, I got a rainbow comin' out of my noggin."_

 **-Reality-**

"Be the ball, feel the ball." Boone said as he got back to his feet, sounding as if he were in a trance.

"He's in the zone." Penn said with excitement, "Good, shoulders back. Now, just listen for the voice to tell you to SWING!"

"Aahh!" Boone yelled in surprise as he struck the ball with great force. The ball went flying forward before bouncing off the side of a tree, off the roof of a passing golf cart, hitting Donald in the head, skipping across a pond like a stone before landing on the green and stopping just on the edge of the hole. Everyone was on the edge of their seats with sweat dripping from their foreheads from the excitement.

"Yes, yes, yes..." Penn chanted.

"No, no, no..." Rippen chanted.

Finally, the ball fell into the hole, causing everyone to cheer at the amazing and improbable shot. Rippen just groaned as he to his knees in defeat.

"Oh, don't worry, Rippen, you and I could still hangout." Larry suggested, causing Rippen to groan even louder.

"Boone Wiseman, you just won the Middleburg Golf Tournament. What are you going to do now?" Donald asked.

"I always wanted to say this." Boone whispered to Penn before getting in front of the crowd, "Hey everybody, we're all gonna get laid!" He yelled, causing the crowd to cheer in excitement.

* * *

 **-Two Weeks Later-**

Penn, Boone, and Sashi arrived at the country club where Crazy Louis let them in.

"Hey guys, how have you been?" He asked.

"We've been great. So, how's that new appendix working out?" Penn asked.

"Oh, funny story about that. Turns out that the appendix is a totally useless organ; so, I sold the appendix you guys won for me and used it to buy... extra thumbs!" He said, showing that he now had four thumbs on his hands, "All rise for the Butter Town anthem! _**Oh Butter Town, we raise our thumbs up high~!**_ Who wants to wrestle?"

"AAAAAHHHHH!" The trio of part-time heroes screamed before running away.

* * *

 **Hope you guys enjoyed this story. Leave a review and give me your thoughts and opinions. See you later!**


End file.
